CAS 920-66-1|1,1,1,3,3,3-Hexafluoro-2-propanol|1,1,1,3,3,3-hexafluoropropan-2-ol|hexafluoroisopropanol|1,1,1,3,3,3-hexafluoropropan-2-ol|HFIP|1,1,1,3,3,3-Hexafluoropropan-2-ol 99.9%|2H-Hexafluoropro...

General Information

Structure

Molecular Formula

C₃H₂F₆O

Molecular Mass

168.0377992

Exact Mass

168.000984

Charge

InChI

InChI=1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10H

InChIKey

BYEAHWXPCBROCE-UHFFFAOYSA-N

Canonic Smiles

OC(C(F)(F)F)C(F)(F)F

Isomeric Smiles

FC(C(C(F)(F)F)O)(F)F

Calculated Properties

JChem

Acid pKa

7.974499

H Acceptors

H Donor

LogD (pH = 5.5)

1.44993

LogD (pH = 7.4)

1.3489344

Log P

1.4513825

Molar Refractivity

18.8317

Polarizability

7.098615

Polar Surface Area

20.23

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1,1,1,3,3,3-Hexafluoro-2-propanolHFIP1,1,1,3,3,3-Hexafluoropropan-2-ol 99.9%2H-Hexafluoropropan-2-ol1,1,1,3,3,3-HEXAFLUORO-ISOPROPANOLHFPHexafluoroisopropanol六氟异丙醇1,1,1,3,3,3-Hexafluoro-2-propanol1,1,1,3,3,3-六氟-2-丙醇1,1,1,3,3,3-Hexafluoropropan-2-ol 99%1,1,1,3,3,3-Hexafluoropropan-2-ol1,1,1,3,3,3-六氟代-2-丙醇1,1,1,3,3,3-Hexafluoroisopropanol

IUPAC name

1,1,1,3,3,3-hexafluoropropan-2-ol

IUPAC Traditional name

hexafluoroisopropanol 1,1,1,3,3,3-hexafluoropropan-2-ol

Names and Identifiers

Registration numbers

Beilstein Number

1841007

PubChem SID

248744762484669524859495160969813

MDL Number

EC Number

CAS Number

PubChem CID

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Apollo Scientific

PC0877

UV absorption < 0.1nm between 200 - 400 nm. Spectrophotometric grade

PC4750

Versatile intermediate, excellent solvent for polymers, hashigh polarity and low nucleophilicity. Ask for references.

MP Biomedicals

02151245

Purity: >99%
1 ml = approx. 1.62 g

Sigma Aldrich

325244

Packaging
5, 25 g in glass bottle
Application
Esterification reagent for the determination of aromatic acids in tissue by GLC and electron capture detection.1Additive which accelerates the Pictet-Spengler synthesis of tetrahydroisoquinolines in water catalyzed by a Bronsted acid-surfactant combined catalyst (BASC).2

105228

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Fluorinated solvent which enhances the efficiency of rhodium(I)-catalyzed [4+2] intramolecular cycloaddition of ether-tethered alkynyl dienes and [5+2] cycloaddition of alkynyl vinylcyclopropanes.1
Solution-phase peptide chemistry solvent.
Packaging
5, 25, 100, 500 g in glass bottle

52512

Other Notes
Solvent with high solubilizing potential for peptides and peptide intermediates1

52517

Other Notes
Size-exclusion chromatography in 1,1,1,3,3,3-hexafluoro-2-propanol1

Molecule Details

References

PubChem Literature

From Data Sources

• The esters formed with N-protected amino acids have been investigated as active intermediates in peptide synthesis: J. Org. Chem., 44, 4577 (1979). See Appendix 6.

• Lithiation generates the useful synthon lithium perfluoropropenolate: Org. Synth., 76, 151 (1998):

• Powerful solvent for oligopeptides: Bull. Chem. Soc. Jpn., 61, 281 (1984); 66, 494 (1993). Used alone as a peptide coupling medium, HFIP gives poor results, but as a cosolvent along with proton acceptors such as DMF, good results, with improved peptide solubility, can be obtained: Tetrahedron Lett., 33, 7007 (1992).

• Effective solvent for uncatalyzed epoxidations of alkenes with H₂O₂ (caution! 60%): Synlett, 248 (2001); or, more conveniently, Urea hydrogen peroxide adduct, L13940: Eur. J. Org. Chem., 3290 (2002). Superior reaction medium for epoxidations, catalyzed by Hexafluoroacetone trihydrate, L10777: Synlett, 1305 (2001). An efficient, selective oxidation of sulfides to sulfoxides with 30% H₂O₂ employs HFIP as solvent, avoiding over-oxidation to the sulfone: Tetrahedron Lett., 39, 3141 (1998). For a review of fluorinated alcohols as solvents for selective and clean reactions, see: Synlett, 18 (2004).

• The mildly acidic character (pK_a 9.3) has been exploited in the selective deprotection of the 4,4'-dimethoxytrityl group in acid-sensitive nucleosides and nucleotides without competing N-glycosyl cleavage: Tetrahedron Lett., 36, 7833 (1995).

• Valuable solvent of high polarity and low nucleophilicity: Tetrahedron Lett., 2335 (1974). Extremely powerful H bond donor but poor H bond acceptor: anions are highly solvated, but cations poorly. For feature article on the use of this unique solvent in the stabilization of radical cations, with particular application to EPR spectroscopy, see: Chem. Commun., 2105 (1996). Preferred solvent for the direct substitution of phenol ethers promoted by [Bis(trifluoroacetoxy)iodo]benzene, L15141: Tetrahedron Lett., 32, 4321 (1991). The intermediacy of radical cations in this reaction has been demonstrated: J. Am. Chem. Soc., 116, 3684 (1994). See also: J. Org. Chem., 60, 7144 (1995).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

1,1,1,3,3,3-hexafluoropropan-2-ol

IUPAC Traditional name

hexafluoroisopropanol 1,1,1,3,3,3-hexafluoropropan-2-ol

Registration numbers

Beilstein Number

1841007

PubChem SID

248744762484669524859495160969813

MDL Number

EC Number

CAS Number

PubChem CID

Molecule Details

PC0877

UV absorption < 0.1nm between 200 - 400 nm. Spectrophotometric grade

PC4750

Versatile intermediate, excellent solvent for polymers, hashigh polarity and low nucleophilicity. Ask for references.

MP Biomedicals

02151245

Purity: >99%
1 ml = approx. 1.62 g

Sigma Aldrich

325244

105228

52512

Other Notes
Solvent with high solubilizing potential for peptides and peptide intermediates1

52517

Other Notes
Size-exclusion chromatography in 1,1,1,3,3,3-hexafluoro-2-propanol1

References

PubChem Literature

From Data Sources

• The esters formed with N-protected amino acids have been investigated as active intermediates in peptide synthesis: J. Org. Chem., 44, 4577 (1979). See Appendix 6.

• Lithiation generates the useful synthon lithium perfluoropropenolate: Org. Synth., 76, 151 (1998):

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:6506